7-bromo-2,4,8,9-tetrazabicyclo[4.3.0]nona-2,4,6,9-tetraen-5-amine

Yellow solid

lH-pyrazolo[3, 4-d]pyrimidin-4-amine (20.0 g, 148.0 mmol) and N- bromosuccinimide (27.7 g, 155.4 mmol) are suspended in DMF (400 ml) and heated to 80°C for 2.5 hrs. After cooling to room temperature, the reaction is quenched with water (dropwise, 800 ml). The precipitate is filtered and suspended in a saturated solution of NaThe mixture of S1 (10 g, 74 mmol) and N-bromosuccinimide(15.8 g, 89 mmol) in DMF (100 mL) was stirred at 80 °C for 8 h. The resulting mixture was allowed to cool to room temperature and then diluted with 300 mL of water. The precipitate was filtered and washed with 2 60 mL of saturated aqueous sodium sulfite, 2 100 mL of water, respectively, and dried under vacuum to yield S2 as a light-yellow solid (10.2 g, 64.4percent), which was used directly without further purification. 1H NMR (300 MHz, DMSO d6) d13.78 (s, 1H), 8.19 (s, 1H), 6.89 (s, 2H)A mixture of 1H-pyrazolo[3, 4-djpyrimidin-4-amine (Formula II, 25 g), Nbromosuccinimide (36.2 g), and dimethylformamide (150 mL) was stirred at 60°C for 4 hours. The reaction mixture was gradually cooled to 25°C to 30°C, and then filtered. Deionized water (750 mL) was added to the filtrate, and the mixture was stirred at 25°C to30°C for 30 minutes. The solid obtained was filtered, then washed with deionized water (50 mL), and then dried under vacuum at 60°C for 10 hours to 12 hours to obtain the title compound.Yield: 27.9 gPreparation of 3-bromo-lH-pyrazolor3.4-dlpyrimidin-4-amine (Formula III, when X is bromine) A mixture of lH-pyrazolo[3, 4-d]pyrimidin-4-amine (Formula II, 25 g), N- bromosuccinimide (36.2 g), and dimethylformamide (150 mL) was stirred at 60°C for 4 hours. The reaction mixture was gradually cooled to room temperature, and then filtered. The filtrate was poured into deionized water (750 mL), and then the mixture was stirred at room temperature for 30 minutes. The solid obtained was filtered, then washed with water (50 mL). The resulting solid was dried at 60°C under vacuum for 10 hours to 12 hours to obtain the title compound. Yield: 27.9 gTo a solution of 4-aminopyrazolo[3, 4-d]pyrimidine (2g) and H2O 25 mL, bromine (2 g) was added dropwise at room temperature, and the mixture was stirred at room temperature for 1 h.Then, it was reacted under reflux for 1 h, dried under reduced pressure, and dissolved in water.The title compound (2.5 g) was obtained.

Molecular Weight:214.02
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:212.96501
Monoisotopic Mass:212.96501
Topological Polar Surface Area:80.5
Heavy Atom Count:11
Complexity:154
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes